CN116867793A - Novel compound and organic light emitting device comprising the same - Google Patents
Novel compound and organic light emitting device comprising the same Download PDFInfo
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- CN116867793A CN116867793A CN202280012327.3A CN202280012327A CN116867793A CN 116867793 A CN116867793 A CN 116867793A CN 202280012327 A CN202280012327 A CN 202280012327A CN 116867793 A CN116867793 A CN 116867793A
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/658—Organoboranes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present disclosure provides novel compounds and organic light emitting devices comprising the same.
Description
Technical Field
Cross Reference to Related Applications
The present application claims the benefit and priority of korean patent application No. 10-2021-0049431, filed on 4-15 of 2021, to the korean intellectual property office, the contents of which are incorporated herein by reference in their entirety.
The present disclosure relates to novel compounds and organic light emitting devices comprising the same.
Background
In general, an organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic material. An organic light emitting device using the organic light emitting phenomenon has characteristics such as a wide viewing angle, excellent contrast, a fast response time, excellent brightness, driving voltage, and response speed, and thus many researches have been conducted.
The organic light emitting device generally has a structure including an anode, a cathode, and an organic material layer interposed between the anode and the cathode. The organic material layer generally has a multi-layered structure including different materials to improve efficiency and stability of the organic light emitting device, for example, the organic material layer may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, if a voltage is applied between two electrodes, holes are injected from an anode into an organic material layer and electrons are injected from a cathode into the organic material layer, and when the injected holes and electrons meet each other, excitons are formed and light is emitted when the excitons fall to a ground state again.
As for the organic materials used in the organic light emitting device as described above, development of new materials is continuously required.
Meanwhile, recently, in order to reduce process costs, organic light emitting devices using a solution method, particularly an inkjet method, instead of a conventional deposition method have been developed. In the initial stage of development, attempts have been made to develop an organic light emitting device by coating all organic light emitting device layers through a solution method, but the current technology has limitations. Therefore, only the HIL, HTL, and EML are processed by the solution method, and a hybrid method using a conventional deposition method as a subsequent method is being studied.
Accordingly, the present disclosure provides new materials for organic light emitting devices that can be used for organic light emitting devices and at the same time can be used for solution processes.
[ Prior Art literature ]
[ patent literature ]
(patent document 1) Korean unexamined patent publication No. 10-2000-0051826
Disclosure of Invention
Technical problem
It is an object of the present disclosure to provide novel compounds and organic light emitting devices comprising the same.
Technical proposal
According to one aspect of the present disclosure, there is provided a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the chemical formula 1, the chemical formula is shown in the drawing,
Ar 1 to furan or thiophene fused to two adjacent rings,
Ar 2 Benzene, benzofuran or benzothiophene condensed with adjacent rings,
each n1 is independently an integer from 1 to 4,
R 1 at least one of which is benzofuranyl or benzothienyl; the remainder being hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 1-60 Alkyl, substituted or unsubstituted C 2-60 Alkenyl, substituted or unsubstituted C 2-60 Alkynyl, substituted or unsubstituted C 3-30 Cycloalkyl, substituted or unsubstituted C 6-60 Aryl, or substituted or unsubstituted C comprising one or more heteroatoms selected from N, O and S 2-60 Heteroaryl, and
R 2 is hydrogen; deuterium; or C which is substituted or unsubstituted 1-60 An alkyl group.
According to another aspect of the present disclosure, there is provided an organic light emitting device including: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprises a compound represented by chemical formula 1.
Advantageous effects
The above-described compound represented by chemical formula 1 may be used as a material of an organic material layer for an organic light emitting device, may be used in a solution process, and may increase efficiency, achieve a low driving voltage, and/or improve lifetime characteristics in the organic light emitting device.
Drawings
Fig. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
Fig. 2 shows an example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron injection and transport layer 8, and a cathode 4.
Detailed Description
Hereinafter, embodiments of the present disclosure will be described in more detail to facilitate understanding of the present invention.
(definition of terms)
As used herein, a symbolMeaning a bond to another substituent.
As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; cyano group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio; arylthio; an alkylsulfonyl group; arylsulfonyl; a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; and heteroaryl containing at least one of N, O and S atoms, or substituted with a substituent that is unsubstituted or linked with two or more of the substituents exemplified above. For example, a "substituent in which two or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl, or it may also be interpreted as a substituent to which two phenyl groups are linked.
In the present disclosure, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the carbonyl group may be a substituent having the following structural formula, but is not limited thereto.
In the present disclosure, the ester group may have a structure in which oxygen of the ester group may be substituted with a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a substituent having the following structural formula, but is not limited thereto.
In the present disclosure, the carbon number of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group may be a substituent having the following structural formula, but is not limited thereto.
In the present disclosure, the silyl group specifically includes, but is not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the like.
In the present disclosure, the boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, and phenylboron group, but is not limited thereto.
In the present disclosure, examples of halogen groups include fluorine, chlorine, bromine, or iodine.
In the present disclosure, the alkyl group may be linear or branched, and the carbon number thereof is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has a carbon number of 1 to 20. According to another embodiment, the alkyl group has a carbon number of 1 to 10. According to another embodiment, the alkyl group has a carbon number of 1 to 6. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present disclosure, the alkenyl group may be linear or branched, and the carbon number thereof is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has a carbon number of 2 to 20. According to another embodiment, the alkenyl group has a carbon number of 2 to 10. According to yet another embodiment, the alkenyl group has a carbon number of 2 to 6. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthalen-1-yl) vinyl-1-yl, 2-bis (diphenyl-1-yl) vinyl-1-yl, Radical, styryl, etc., but is not limited thereto.
In the present disclosure, the cycloalkyl group is not particularly limited, but the carbon number thereof is preferably 3 to 60. According to one embodiment, the cycloalkyl group has a carbon number of 3 to 30. According to another embodiment, the cycloalkyl group has a carbon number of 3 to 20. According to yet another embodiment, the cycloalkyl group has a carbon number of 3 to 6. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-t-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.
In the present disclosure, the aryl group is not particularly limited, but the carbon number thereof is preferably 6 to 60, and it may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has a carbon number of 6 to 30. According to one embodiment, the aryl group has a carbon number of 6 to 20. As the monocyclic aryl group, an aryl group may be phenyl, biphenyl, terphenyl, or the like, but is not limited thereto. Polycyclic aryl groups include naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl,A radical, a fluorenyl radical, etc., but is not limited thereto.
In the present disclosure, the fluorenyl group may be substituted, and two substituents may be linked to each other to form a spiro structure. In the case where the fluorenyl group is substituted, it may be formed Etc. However, the structure is not limited thereto.
In the present disclosure, the heteroaryl group is a heteroaryl group including at least one of O, N, si and S as a heteroatom, and the carbon number thereof is not particularly limited, but is preferably 2 to 60. Examples of heteroaryl groups include xanthenyl, thioxanthenyl, thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl,Azolyl, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthrolinyl, and i ∈ ->Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present disclosure, the aryl groups in the aralkyl group, the aralkenyl group, the alkylaryl group, the arylamine group, and the arylsilyl group are the same as the above examples of the aryl groups. In the present disclosure, the alkyl groups in the aralkyl group, alkylaryl group, and alkylamino group are the same as the above examples of the alkyl group. In the present disclosure, heteroaryl groups in heteroaryl amines may employ the above description of heteroaryl groups. In the present disclosure, alkenyl groups in aralkenyl groups are the same as the above examples of alkenyl groups. In the present disclosure, the above description of aryl groups may be applied, except that arylene groups are divalent groups. In the present disclosure, the above description of heteroaryl groups may be applied, except that the heteroarylene group is a divalent group. In the present disclosure, the above description of aryl or cycloalkyl groups may be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In the present disclosure, the above description of heteroaryl groups may be applied, except that the heterocycle is not a monovalent group but is formed by combining two substituents.
(Compound)
The present disclosure provides a compound represented by chemical formula 1.
The compound represented by chemical formula 1 is characterized by containing at least one benzofuranyl or benzothienyl group in its molecular structure, whereby it not only has solubility suitable for a solution method, but also its synthesis is easy. In addition, when the compound is used to manufacture an organic light emitting device, the efficiency of the organic light emitting device is improved, and the lifetime is also significantly improved.
Preferably, benzofuranyl is benzofuran-2-ylOr benzofuran-3-ylBenzothienyl is benzothien-2-yl +.>Or benzothien-3-yl
Preferably, chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
In chemical formulas 1-1 to 1-4,
Ar 2 、n1、R 1 and R is 2 As defined above.
Preferably, R 1 At least one of which is And the remainder are hydrogen, deuterium, substituted or unsubstituted C 1-60 Alkyl, substituted or unsubstituted C 6-60 Aryl, or substituted or unsubstituted C comprising one or more heteroatoms selected from N, O and S 2-60 Heteroaryl groups.
Preferably, R 1 At least one of which is The balance being hydrogen, deuterium, C 3-10 Alkyl, phenyl, dibenzofuranyl or dibenzothienyl.
Preferably, R 1 At least one of which is And the remainder are hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, dibenzofuranyl or dibenzothiophenyl.
Preferably, R 2 Is hydrogen, deuterium or C 1-4 An alkyl group.
Preferably, R 2 Is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl.
Representative examples of the compound represented by chemical formula 1 are as follows.
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Meanwhile, the present disclosure provides a method for preparing the compound represented by chemical formula 1, as shown in the following reaction scheme 1 as an example.
Reaction scheme 1
In reaction scheme 1, the definition of the remaining substituents other than X is the same as defined above, and X is halogen, preferably bromine or chlorine.
Step 1 is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the amine substitution reaction may be varied as known in the art. Step 2 is with BI 3 Preferably in the presence of a base. The above preparation method may be further embodied in the preparation examples described below.
Meanwhile, the organic material layer including the compound according to the present disclosure may be formed using various methods such as a vacuum deposition method and a solution method, and the solution method will be described in detail below.
(coating composition)
The compound according to the present disclosure may form an organic material layer of an organic light emitting device, particularly a light emitting layer, by a solution process. For this purpose, the present disclosure provides a coating composition comprising the above-described compound according to the present disclosure and a solvent.
The solvent is not particularly limited as long as it is a solvent capable of dissolving or dispersing the compound according to the present disclosure. Examples of the solvent may include: chlorine-based solvents such as chloroform, methylene chloride, 1, 2-dichloroethane, 1, 2-trichloroethane, chlorobenzene and o-dichlorobenzene; ether-based solvents, e.g. tetrahydrofuran and diAn alkane; solvents based on aromatic hydrocarbons, such as toluene, xylene, trimethylbenzene, and mesitylene; solvents based on aliphatic hydrocarbons, e.g. cyclohexane, methylcyclohexane, n-pentaneHexane, n-heptane, n-octane, n-nonane and n-decane; ketone-based solvents such as acetone, methyl ethyl ketone, and cyclohexanone; ester-based solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; polyhydric alcohols such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerol and 1, 2-hexanediol, and derivatives thereof; alcohol-based solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide-based solvents, such as dimethyl sulfoxide; amide-based solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide; benzoate-based solvents, such as butyl benzoate and methyl 2-methoxybenzoate; tetralin; 3-phenoxy-toluene; etc. Further, the above solvents may be used alone or in combination of two or more solvents.
In addition, the coating composition may further contain a compound serving as a host material, and details of the compound serving as a host material will be described later. Further, the coating composition may contain a compound used as a dopant material, and the compound used for the dopant material will be described later.
Further, the viscosity of the coating composition is preferably 1cP or more. Further, in view of easiness of application of the coating composition, the viscosity of the coating composition is preferably 10cP or less. Further, the concentration of the compound according to the present disclosure in the coating composition is preferably 0.1 wt/vol% or more. Further, the concentration of the compound according to the present disclosure in the coating composition is preferably 20 wt/vol% or less so that the coating composition is optimally coated.
In another embodiment of the present disclosure, a method for forming a light emitting layer using the above-described coating composition is provided. Specifically, the method comprises the steps of: coating the above-described light emitting layer according to the present disclosure on the anode or the hole transporting layer by a solution method; and heat treating the applied coating composition.
The solution method uses the above-described coating composition according to the present disclosure, and refers to spin coating, dip coating, blade coating, ink jet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
The heat treatment temperature in the heat treatment step is preferably 150 ℃ to 230 ℃. Further, the heat treatment time may be 1 minute to 3 hours, more preferably 10 minutes to 1 hour. In addition, the heat treatment is preferably performed in an inert gas atmosphere such as argon and nitrogen.
(organic light-emitting device)
In another embodiment of the present disclosure, an organic light emitting device including the compound represented by chemical formula 1 is provided. In one example, the present disclosure provides an organic light emitting device comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprises a compound represented by chemical formula 1.
The organic material layer of the organic light emitting device of the present disclosure may have a single layer structure, or it may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present disclosure may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and it may include a smaller number of organic layers.
Further, the organic material layer may include a light emitting layer, wherein the light emitting layer may include a compound represented by chemical formula 1. In particular, compounds according to the present disclosure may be used as dopants for light emitting layers.
Further, the organic light emitting device according to the present disclosure may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present disclosure may be an inverted organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting device according to an embodiment of the present disclosure is shown in fig. 1 and 2.
Fig. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In such a structure, the compound represented by chemical formula 1 may be included in the light emitting layer.
Fig. 2 shows an example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron injection and transport layer 8, and a cathode 4. In such a structure, the compound represented by chemical formula 1 may be included in the light emitting layer.
The organic light emitting device according to the present disclosure may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes a compound represented by chemical formula 1. In addition, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
For example, an organic light emitting device according to the present disclosure may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. In this case, the organic light emitting device may be manufactured by: depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method to form an anode; forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode; a material that can be used as a cathode is then deposited on the organic material layer.
In addition to such a method, the organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (international publication WO 2003/012890). However, the manufacturing method is not limited thereto.
In one example, the first electrode is an anode and the second electrode is a cathode, or alternatively, the first electrode is a cathode and the second electrode is an anode.
As the anode material, it is generally preferable to use a material having a large work function so that holes can be formedAnd smoothly injected into the organic material layer. Specific examples of the anode material include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, e.g. ZnO, al or SnO 2 Sb; conductive compounds, e.g. poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDOT), polypyrrole, and polyaniline; etc., but is not limited thereto.
As the cathode material, it is generally preferable to use a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of the cathode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structural materials, e.g. LiF/Al or LiO 2 Al; etc., but is not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound of: it has a capability of transporting holes, and thus has an effect of injecting holes in an anode, and has an excellent hole injection effect to a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from moving to an electron injection layer or an electron injection material, and is also excellent in the capability of forming a thin film. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metalloporphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazabenzophenanthrene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline-based and polythiophene-based conductive polymer, and the like, but are not limited thereto.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole transport material is suitably a material having a large hole mobility, which can receive holes from the anode or the hole injection layer and transfer the holes to the light emitting layer. Specific examples thereof include an arylamine-based organic material, a conductive compound, a block copolymer in which a conjugated moiety and a non-conjugated moiety are simultaneously present, and the like, but are not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material may be a fused aromatic ring derivative, a heterocyclic ring-containing compound, or the like. Specific examples of the condensed aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like. Examples of the heterocycle-containing compound include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
Examples of dopant materials include aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is a substituted or unsubstituted fused aromatic ring derivative having an arylamino group, and examples thereof include pyrene having an arylamino group, anthracene, Bisindenopyrene, and the like. The styrylamine compound is a compound in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, wherein one or two or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamino groups are substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styrylenediamine, styrylenetriamine, styrenetetramine, and the like. Further, the metal complex includes iridium complex, platinum complex, and the like, but is not limited thereto.
The electron injection and transport layer is a layer for simultaneously functioning as an electron transport layer and an electron injection layer injecting electrons from the electrode and transporting the received electrons up to the light emitting layer, and is formed on the light emitting layer or the electron adjusting layer. The electron injecting and transporting material is suitably a material that can well receive electrons from the cathode and transfer the electrons to the light emitting layer, and has a large electron mobility. Specific examples of the electron injecting and transporting material include: al complexes of 8-hydroxyquinoline; comprising Alq 3 Is a complex of (a) and (b); an organic radical compound; hydroxy groupFlavone-metal complexes, triazine derivatives, and the like, but are not limited thereto. Alternatively, liF, naF, naCl, csF, li can be used 2 O, baO fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,Azole,/->Diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex compound include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (2-methyl-8-quinoline) chlorogallium, gallium bis (2-methyl-8-quinoline) (o-cresol), aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol), and the like.
The light emitting layer, the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer may contain inorganic compounds such as quantum dots or polymer compounds in addition to the above materials.
The quantum dots may be, for example, colloidal quantum dots, alloy quantum dots, core-shell quantum dots, or core quantum dots. The quantum dot may be a quantum dot including an element belonging to group 2 and group 16, an element belonging to group 13 and group 15, an element belonging to group 13 and group 17, an element belonging to group 11 and group 17, or an element belonging to group 14 and group 15. Quantum dots containing elements such As cadmium (Cd), selenium (Se), zinc (Zn), sulfur (S), phosphorus (P), indium (In), tellurium (Te), lead (Pb), gallium (Ga), or arsenic (As) may be used.
The organic light emitting device according to the present disclosure may be a bottom light emitting device, a top light emitting device, or a double-sided light emitting device, and in particular, may be a bottom light emitting device requiring relatively high light emitting efficiency.
Further, the compound according to the present disclosure may be contained in an organic solar cell or an organic transistor in addition to an organic light emitting device.
The preparation of the compound represented by chemical formula 1 and the organic light emitting device including the same will be specifically described in the following examples. However, the following examples are provided for illustrative purposes only and are not intended to limit the scope of the present disclosure.
Examples
Example 1: preparation of Compound 1
Compounds 1-a (1.0 eq), naOt-Bu (4 eq) and 1-b (1.05 eq) were placed in a round bottom flask and dissolved in anhydrous toluene (0.1M). Pd (t-Bu) was added dropwise thereto at a bath temperature of 100 ℃ 3 P) 2 (5 mol%) and the mixture was stirred for 2 hours. After the reaction, the reaction mixture was cooled at room temperature, using CH 2 Cl 2 Sufficiently diluted and then used with CH 2 Cl 2 Washing with brine. The organic layer was separated with MgSO 4 The water was removed and passed through a Celite-Florisil-Silica pad. The resulting solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound 1-c (yield: 76%).
Compound 1-d (1.0 eq), naOt-Bu (4 eq) and compound 1-c (1.05 eq) were placed in a round bottom flask and dissolved in anhydrous toluene (0.1M). Pd (t-Bu) was added dropwise thereto at a bath temperature of 120 ℃ 3 P) 2 (5 mol%) and the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled at room temperature, using CH 2 Cl 2 Sufficiently diluted and then used with CH 2 Cl 2 Washing with brine. The organic layer was separated with MgSO 4 The water was removed and passed through a celite-florisil-silica pad. Concentrating the obtained solution under reduced pressure, and purifying by column chromatographyCompound 1-e (yield: 81%).
Compound 1-f (1.0 eq) and compound 1-g (1.05 eq) were placed in a round bottom flask and dissolved in anhydrous THF (0.1M). K is added dropwise to the reaction solution 2 CO 3 (aqueous solution) (1.5 eq). Pd (PPh) was added dropwise thereto at a bath temperature of 80 ℃ 3 ) 4 (1.5 mol%) and the mixture was stirred for 2 hours. After the reaction, the reaction mixture was cooled at room temperature, using CH 2 Cl 2 Sufficiently diluted and then used with CH 2 Cl 2 Washing with brine. The organic layer was separated with MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resulting solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound 1-h (yield: 62%).
Compound 1-h (1.0 eq), naOt-Bu (4 eq) and compound 1-i (1.05 eq) were placed in a round bottom flask and dissolved in anhydrous toluene (0.1M). Pd (t-Bu) was added dropwise thereto at a bath temperature of 100 ℃ 3 P) 2 (5 mol%) and the mixture was stirred for 2 hours. After the reaction, the reaction mixture was cooled at room temperature, using CH 2 Cl 2 Sufficiently diluted and then used with CH 2 Cl 2 Washing with brine. The organic layer was separated with MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resulting solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound 1-j (yield: 76%).
Compound 1-e (1.0 eq), naOt-Bu (4 eq) and compound 1-j (1.05 eq) were placed in a round bottom flask and dissolved in anhydrous toluene (0.1M). Pd (t-Bu) was added dropwise thereto at a bath temperature of 100 ℃ 3 P) 2 (5 mol%) and the mixture was stirred overnight. After the reaction, the reaction mixture was cooled at room temperature, using CH 2 Cl 2 Sufficiently diluted and then used with CH 2 Cl 2 Washing with brine. The organic layer was separated with MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resulting solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound 1-k (yield: 71%).
Compound 1-k (1.0 eq) was placed in a round bottom flask and dissolved in anhydrous toluene (0.03M). To which BI is added dropwise 3 (2.0 eq.) and the mixture was stirred at 80℃bath temperature overnight. After the reaction, the reaction mixture was cooled at room temperature and taken up with CH 2 Cl 2 And (5) fully diluting. Sequentially dropwise adding EtNi-Pr into the reaction mixture 2 (15.0 eq.) and saturated Na 2 S 2 O 3 (aqueous solution) using CH 2 Cl 2 Brine wash and separate the organic layer. With MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resultant solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound 1 (yield: 71%).
m/z[M+H] + 863.5
Example 2: preparation of Compound 2
Compound 2 was produced in the same manner as in the production method of compound 1, except that compound 2-a was used instead of compound 1-f.
m/z[M+H] + 863.4
Example 3: preparation of Compound 3
Compound 3 was produced in the same manner as in the production method of compound 1, except that compound 3-a was used instead of compound 1-f, and compound 3-c was used instead of compound 1-i.
m/z[M+H] + 815.5
Example 4: preparation of Compound 4
Compound 4 was produced in the same manner as in the production method of compound 1, except that compound 4-a was used instead of compound 1-f.
m/z[M+H] + 847.6
Example 5: preparation of Compound 5
Compound 5 was produced in the same manner as in the production method of compound 1, except that compound 5-a was used instead of compound 1-a.
m/z[M+H] + 848.4
Example 6: preparation of Compound 6
Compound 6 was produced in the same manner as in the production method of compound 5, except that compound 2-c was used instead of compound 1-j.
m/z[M+H] + 879.4
Example 7: preparation of Compound 7
Compound 7 was produced in the same manner as in the production method of compound 5, except that compound 3-d was used instead of compound 1-j.
m/z[M+H] + 831.4
Example 8: preparation of Compound 8
Compound 8 was produced in the same manner as in the production method of compound 5, except that compound 4-b was used instead of compound 1-j.
m/z[M+H] + 863.4
Example 9: preparation of Compound 9
Compound 9 was produced in the same manner as in the production method of compound 1, except that compound 9-a was used instead of compound 1-a.
m/z[M+H] + 863.5
Example 10: preparation of Compound 10
Compound 10 was produced in the same manner as in the production method of compound 1, except that compound 10-a was used instead of compound 1-a.
m/z[M+H] + 879.2
Example 11: preparation of Compound 11
Compound 3-b (1.0 eq), naOt-Bu (4 eq) and compound 11-a (1.05 eq) were placed in a round bottom flask and dissolved in anhydrous toluene (0.1M). Pd (t-Bu) was added dropwise thereto at a bath temperature of 100 ℃ 3 P) 2 (5 mol%) and the mixture was stirred for 2 hours. After the reaction, the reaction mixture was cooled at room temperature, using CH 2 Cl 2 Sufficiently diluted and then used with CH 2 Cl 2 Washing with brine. The organic layer was separated with MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resulting solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound 11-b (yield: 81%).
Compound 11-c (1.0 eq.) and NaOt-Bu (4 eq) and Compound 11-a (1.05 eq) were placed in a round bottom flask and dissolved in anhydrous toluene (0.1M). Pd (t-Bu) was added dropwise thereto at a bath temperature of 100 ℃ 3 P) 2 (5 mol%) and the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled at room temperature, using CH 2 Cl 2 Sufficiently diluted and then used with CH 2 Cl 2 Washing with brine. The organic layer was separated with MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resulting solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound 11-d (yield: 79%).
Compounds 11-d (1.0 eq.) were placed in a round bottom flask and dissolved in anhydrous toluene (0.03M). To which BI is added dropwise 3 (2.0 eq.) and the mixture was stirred at 80℃bath temperature overnight. After the reaction, the reaction mixture was cooled sufficiently at room temperature and was quenched with CH 2 Cl 2 And (5) diluting. Sequentially dropwise adding EtNi-Pr into the reaction mixture 2 (15.0 eq.) and saturated Na 2 S 2 O 3 (aqueous solution) using CH 2 Cl 2 Brine wash and separate the organic layer. With MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resultant solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound 11 (yield: 72%).
m/z[M+H] + 915.2
Example 12: preparation of Compound 12
Compound 1-f (1.0 eq) and compound 1-g (2.05 eq) were placed in a round bottom flask and dissolved in anhydrous THF (0.1M). K is added dropwise to the reaction solution 2 CO 3 (aqueous solution) (3 eq). Pd (PPh) was added dropwise thereto at a bath temperature of 80 ℃ 3 ) 4 (3 mol%) and the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled at room temperature, using CH 2 Cl 2 Sufficiently diluted and then used with CH 2 Cl 2 Washing with brine. The organic layer was separated with MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resulting solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound 12-b (yield: 78%).
Compound 1-a (1.0 eq), naOt-Bu (4 eq) and compound 12-b (1.05 eq) were placed in a round bottom flask and dissolved in anhydrous toluene (0.1M). Pd (t-Bu) was added dropwise thereto at a bath temperature of 100 ℃ 3 P) 2 (5 mol%) and the mixture was stirred for 2 hours. After the reaction, the reaction mixture was cooled at room temperature, using CH 2 Cl 2 Sufficiently diluted and then used with CH 2 Cl 2 Washing with brine. The organic layer was separated with MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resulting solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound 12-c (yield: 82%).
Then, compound 12 was produced in the same manner as in the production method of compound 1, except that compound 12-c was used instead of compound 1-j.
m/z[M+H] + 943.6
Example 13: preparation of Compound 13
Compound 13 was produced in the same manner as in the production method of compound 11, except that compound 12-c was used instead of compound 11-b.
m/z[M+H] + 1091.2
Example 14: preparation of Compound 14
The compound 5-a (1.0 eq), naOt-Bu (4 eq) and compound 12-b (1.05 eq) were placed inIn a round bottom flask and was dissolved in anhydrous toluene (0.1M). Pd (t-Bu) was added dropwise thereto at a bath temperature of 100 ℃ 3 P) 2 (5 mol%) and the mixture was stirred for 2 hours. After the reaction, the reaction mixture was cooled at room temperature, using CH 2 Cl 2 Sufficiently diluted and then used with CH 2 Cl 2 Washing with brine. The organic layer was separated with MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resulting solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound 14-a (yield: 87%).
Then, compound 14 was produced in the same manner as in the production method of compound 13, except that compound 14-a was used instead of compound 12-c.
m/z[M+H] + 1123.5
Example 15: preparation of Compound 15
Compound 1-f (1.0 eq) and compound 15-a (1.05 eq) were placed in a round bottom flask and dissolved in anhydrous THF (0.1M). K is added dropwise to the reaction solution 2 CO 3 (aqueous solution) (1.5 eq). Pd (PPh) was added dropwise thereto at a bath temperature of 80 ℃ 3 ) 4 (1.5 mol%) and the mixture was stirred for 2 hours. After the reaction, the reaction mixture was cooled at room temperature, using CH 2 Cl 2 Sufficiently diluted and then used with CH 2 Cl 2 Washing with brine. The organic layer was separated with MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resulting solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound 15-b (yield: 67%).
Compound 15-b (1.0 eq), naOt-Bu (4 eq) and compound 1-i (1.05 eq) were placed in a round bottom flask and dissolved in anhydrous toluene (0.1M). Pd (t-Bu) was added dropwise thereto at a bath temperature of 100 ℃ 3 P) 2 (5 mol%) and the mixture was stirred for 2 hours. In the reactionAfter that, the reaction mixture was cooled at room temperature, and taken up with CH 2 Cl 2 Sufficiently diluted and then used with CH 2 Cl 2 Washing with brine. The organic layer was separated with MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resulting solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound 15-c (yield: 72%).
Compounds 1-d (1.0 eq), naOt-Bu (4 eq) and compound 15-c (1.05 eq) were placed in a round bottom flask and dissolved in anhydrous toluene (0.1M). Pd (t-Bu) was added dropwise thereto at a bath temperature of 120 ℃ 3 P) 2 (5 mol%) and the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled at room temperature, using CH 2 Cl 2 Sufficiently diluted and then used with CH 2 Cl 2 Washing with brine. The organic layer was separated with MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resulting solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound 15-d (yield: 77%).
Compound 15-d (1.0 eq), naOt-Bu (4 eq) and compound 1-c (1.05 eq) were placed in a round bottom flask and dissolved in anhydrous toluene (0.1M). Pd (t-Bu) was added dropwise thereto at a bath temperature of 100 ℃ 3 P) 2 (5 mol%) and the mixture was stirred overnight. After the reaction, the reaction mixture was cooled at room temperature, using CH 2 Cl 2 Sufficiently diluted and then used with CH 2 Cl 2 Washing with brine. The organic layer was separated with MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resulting solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound 15-e (yield: 75%).
Compound 15-e (1.0 eq) was placed in a round bottom flask and dissolved in anhydrous toluene (0.03M). To which BI is added dropwise 3 (2.0 eq.) the mixture was stirred at 80℃bath temperature overnight. After the reaction, the reaction mixture was cooled at room temperature and taken up with CH 2 Cl 2 And (5) fully diluting. Sequentially dropwise adding EtNi-Pr into the reaction mixture 2 (15.0 eq.) and saturated Na 2 S 2 O 3 (aqueous solution) using CH 2 Cl 2 Brine wash and separate the organic layer. With MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resultant solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound 15 (yield: 78%).
m/z[M+H] + 879.5
Example 16: preparation of Compound 16
Compound 16 was produced in the same manner as in the production method of compound 15, except that compound 5-b was used instead of compound 1-c.
m/z[M+H] + 895.6
Example 17: preparation of Compound 17
Compound 17 was produced in the same manner as in the production method of compound 12, except that compound 15-a was used instead of compound 1-g.
m/z[M+H] + 1155.2
Example 18: preparation of Compound 18
Compound 18 was produced in the same manner as in the production method of compound 17, except that compound 5-a was used instead of compound 1-a.
m/z[M+H] + 1187.3
Comparative example
Comparative example 1: preparation of Compound F
Compound 1-d (1.0 eq), naOt-Bu (4.0 eq) and compound F-a (2.05 eq) were placed in a round bottom flask and dissolved in anhydrous toluene (0.1M). Pd (t-Bu) was added dropwise thereto at a bath temperature of 120 ℃ 3 P) 2 (5 mol%) and the mixture was stirred overnight. After the reaction, the reaction mixture was cooled at room temperature, using CH 2 Cl 2 Sufficiently diluted and then used with CH 2 Cl 2 Washing with brine. The organic layer was separated with MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resulting solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound F-b (yield: 75%).
Compound F-b (1.0 eq) was placed in a round bottom flask and dissolved in anhydrous toluene (0.03M). To which BI is added dropwise 3 (2.0 eq.) and the mixture was stirred at 80℃bath temperature overnight. After the reaction, the reaction mixture was cooled at room temperature and taken up with CH 2 Cl 2 And (5) fully diluting. Sequentially dropwise adding EtNi-Pr into the reaction mixture 2 (15.0 eq.) and saturated Na 2 S 2 O 3 (aqueous solution) using CH 2 Cl 2 Brine wash and separate the organic layer. With MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resultant solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound F (yield: 87%).
m/z[M+H] + ＝659.6
Comparative example 2: preparation of Compound G
Compound G was prepared in the same manner as in the preparation method of comparative example 1, except that compound G-a was used instead of compound F-a.
m/z[M+H] + ＝659.5
Comparative example 3: preparation of Compound H
Compounds H-a (1.0 eq), naOt-Bu (4.0 eq) and H-b (1.05 eq) were placed in a round-bottomed flask and dissolved in anhydrous toluene (0.1M). Pd (t-Bu) was added dropwise thereto at a bath temperature of 120 ℃ 3 P) 2 (5 mol%) and the mixture was stirred overnight. After the reaction, the reaction mixture was cooled at room temperature, using CH 2 Cl 2 Sufficiently diluted and then used with CH 2 Cl 2 Washing with brine. The organic layer was separated with MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resulting solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound H-c (yield: 79%).
Compound H-c (1.0 eq) was placed in a round bottom flask and dissolved in anhydrous toluene (0.03M). To which BI is added dropwise 3 (2.0 eq.) and the mixture was stirred at 80℃bath temperature overnight. After the reaction, the reaction mixture was cooled at room temperature and taken up with CH 2 Cl 2 And (5) fully diluting. Sequentially dropwise adding EtNi-Pr into the reaction mixture 2 (15.0 eq.) and saturated Na 2 S 2 O 3 (aqueous solution) using CH 2 Cl 2 Brine wash and separate the organic layer. With MgSO 4 The water was removed and passed through a celite-florisil-silica pad. The resultant solution was concentrated under reduced pressure, followed by purification by column chromatography to prepare compound H (yield: 73%).
m/z[M+H] + ＝725.5
Experimental example
Experimental example 1
Coated with a coating having a thickness ofThe ITO (indium tin oxide) as a thin film is put into a distillation column in which a cleaning agent is dissolvedIn water, and ultrasonic cleaning is performed. At this time, a product manufactured by Fischer co. Was used as a detergent, and distilled water filtered twice using a filter manufactured by Millipore co. Was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice using distilled water for 10 minutes. After the washing with distilled water was completed, the substrate was ultrasonically washed with isopropanol, acetone and methanol solvents, dried, and then the substrate was washed for 5 minutes, and then transferred to a glove box.
Spin-coating (4000 rpm) a coating composition in which the following compound O and compound P (weight ratio of 2:8) were dissolved in cyclohexanone at 20 wt/vol% on an ITO transparent electrode, and heat-treating (curing) at 200 ℃ for 30 minutes to form a coating film having a thickness ofIs provided. Spin-coating (4000 rpm) a coating composition in which the following compound Q (Mn: 27,900; mw:35,600; measured by GPC (Agilent 1200 series) using a PC standard) was dissolved in toluene at 6% by weight/volume was applied on the hole injection layer, and heat-treating at 200℃for 30 minutes to form a coating composition having a thickness of ±%>Is provided. Coating composition in which previously prepared compound 1 and the following compound R (weight ratio of 2:98) were dissolved in cyclohexanone at 2 wt/vol% was spin-coated (4000 rpm) on the hole transport layer, and heat-treated at 180 ℃ for 30 minutes to form a thickness ofIs provided. After transfer to the vacuum evaporator, the following compounds S to +.> To form an electron injection and transport layer. Sequentially on electron injection and transport layersDeposition->And aluminumTo form a cathode. />
In the above process, the vapor deposition rate of the organic material is maintained atSecond to->Per second, the deposition rate of LiF is kept +. >Per second, the deposition rate of aluminum is kept +.>Per second, and maintaining the vacuum level during deposition at 2 x 10 -7 To 5 x 10 -8 And (5) a bracket.
Experimental examples 2 to 18
An organic light-emitting device was manufactured in the same manner as in experimental example 1, except that the compound shown in table 1 below was used instead of the compound 1.
Comparative examples 1 to 3
An organic light-emitting device was manufactured in the same manner as in experimental example 1, except that the compound shown in table 1 below was used instead of the compound 1.
By applying 10mA/cm to the organic light emitting devices manufactured in the experimental examples and the comparative experimental examples 2 The driving voltage, external Quantum Efficiency (EQE), and lifetime were measured, and the results are shown in table 1 below. At this time, the External Quantum Efficiency (EQE) is calculated as "(number of emitted photons)/(injection)Number of charge carriers in) 100", and T90 means the time required for the luminance to decrease to 90% of the initial luminance (500 nit).
TABLE 1
As shown in table 1 above, the organic light emitting device including the compound of the present disclosure as a dopant of the light emitting layer exhibits excellent characteristics in terms of efficiency, driving voltage, and lifetime.
< description of reference numerals >
1: substrate 2: anode
3: light emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: light emitting layer 8: electron injection and transport layers
Claims (10)
1. A compound represented by the following chemical formula 1:
[ chemical formula 1]
In the chemical formula 1, the chemical formula is shown in the drawing,
Ar 1 to furan or thiophene fused to two adjacent rings,
Ar 2 benzene, benzofuran or benzothiophene condensed with adjacent rings,
each n1 is independently an integer from 1 to 4,
R 1 at least one of which is benzofuranyl or benzothienyl; the remainder being hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 1-60 Alkyl, substituted or unsubstituted C 2-60 Alkenyl, substituted or unsubstituted C 2-60 Alkynyl, substituted or unsubstituted C 3-30 Cycloalkyl, substituted or unsubstituted C 6-60 Aryl, or substituted or unsubstituted packageC containing one or more hetero atoms selected from N, O and S 2-60 Heteroaryl, and
R 2 is hydrogen; deuterium; or C which is substituted or unsubstituted 1-60 An alkyl group.
2. A compound according to claim 1, wherein:
the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
In chemical formulas 1-1 to 1-4,
Ar 2 、n1、R 1 and R is 2 As defined in claim 1.
3. A compound according to claim 1, wherein:
R 1 At least one of which isThe balance being hydrogen, deuterium, substituted or unsubstitutedC of (2) 1-60 Alkyl, substituted or unsubstituted C 6-60 Aryl, or substituted or unsubstituted C comprising one or more heteroatoms selected from N, O and S 2-60 Heteroaryl groups.
4. A compound according to claim 1, wherein:
R 1 at least one of which isThe balance being hydrogen, deuterium, C 3-10 Alkyl, phenyl, dibenzofuranyl or dibenzothienyl.
5. A compound according to claim 1, wherein:
R 1 at least one of which isAnd the remainder are hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, dibenzofuranyl or dibenzothiophenyl.
6. A compound according to claim 1, wherein:
R 2 is hydrogen, deuterium or C 1-4 An alkyl group.
7. A compound according to claim 1, wherein:
R 2 is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl.
8. A compound according to claim 1, wherein:
the compound represented by chemical formula 1 is any one selected from the group consisting of:
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9. an organic light emitting device comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the compound according to any one of claims 1 to 8.
10. The organic light-emitting device of claim 9, wherein:
the organic material layer including the compound is a light emitting layer.
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| PCT/KR2022/004566 WO2022220453A1 (en) | 2021-04-15 | 2022-03-31 | Novel compound and organic light-emitting device comprising same |
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| DE10135513B4 (en) | 2001-07-20 | 2005-02-24 | Novaled Gmbh | Light-emitting component with organic layers |
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